US5612396A - Copolymers - Google Patents
Copolymers Download PDFInfo
- Publication number
- US5612396A US5612396A US08/471,544 US47154495A US5612396A US 5612396 A US5612396 A US 5612396A US 47154495 A US47154495 A US 47154495A US 5612396 A US5612396 A US 5612396A
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- alkyl
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- random copolymer
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 27
- -1 polysiloxane Polymers 0.000 claims abstract description 20
- 229920005604 random copolymer Polymers 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 12
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 9
- 150000003839 salts Chemical group 0.000 claims abstract description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 16
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000004568 cement Substances 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 9
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- 229910001413 alkali metal ion Inorganic materials 0.000 claims description 4
- 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 4
- 229910001448 ferrous ion Inorganic materials 0.000 claims description 4
- 229920001451 polypropylene glycol Polymers 0.000 claims description 3
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000012615 aggregate Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 229920001281 polyalkylene Polymers 0.000 claims 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 abstract description 4
- 239000000178 monomer Substances 0.000 abstract description 2
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 abstract 1
- 101150035983 str1 gene Proteins 0.000 abstract 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 11
- 229940117927 ethylene oxide Drugs 0.000 description 10
- 239000004698 Polyethylene Substances 0.000 description 7
- 239000004567 concrete Substances 0.000 description 7
- 239000004570 mortar (masonry) Substances 0.000 description 7
- 229920001983 poloxamer Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 229920001400 block copolymer Polymers 0.000 description 5
- 239000011398 Portland cement Substances 0.000 description 4
- 229920004482 WACKER® Polymers 0.000 description 4
- 125000002947 alkylene group Chemical group 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- DOKHEARVIDLSFF-UHFFFAOYSA-N prop-1-en-1-ol Chemical group CC=CO DOKHEARVIDLSFF-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008399 tap water Substances 0.000 description 2
- 235000020679 tap water Nutrition 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 101150108015 STR6 gene Proteins 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005376 alkyl siloxane group Chemical group 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 159000000013 aluminium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 125000001142 dicarboxylic acid group Chemical group 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 1
- 229960003505 mequinol Drugs 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229960002796 polystyrene sulfonate Drugs 0.000 description 1
- 239000011970 polystyrene sulfonate Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000002893 slag Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
Definitions
- This invention is concerned with new organic copolymers which can be used as additives to cementitious mixes.
- the invention relates to a random copolymer in free acid or salt form having the following types and numbers of monomer units; ##STR2## in which M is hydrogen or the residue of a hydrophobic polyalkylene glycol or polysiloxane,
- R is an C 2-6 alkylene radical
- R 1 is a C 1-20 alkyl , C 6-9 cycloalkyl or phenyl group,
- x,y and z are numbers from 1 to 100
- n is a number from 1 to 100
- n is a number from 10 to 100
- the organic copolymers of styrene and maleic acid half ester preferably have a weight average molecular weight from 5,000 to 100,000 more preferably from 10,000 to 30,000 and preferably have an even distribution of styrene and maleic acid half ester units, i.e. the ratio of x to (y+z) is from 1:3 to 3:1, most preferably the ratio of x to (y+z) is 1:1. Most preferred copolymers have a weight average molecular weight of about 13,000.
- the weight average molecular weight (Mw) is determined by HPLC (high pressure liquid chromatography) analysis using a polystyrene sulfonate standard.
- any alkyl or alkylene groups may be linear or branched and each R, independently, is preferably a C 2-3 alkylene group, most preferably each R is the same and is ethylene.
- Each R 1 independently, is preferably C 1-2 alkyl, more preferably all groups R 1 are methyl.
- m preferably is a number from 7 to 20, most preferably 10-15.
- M is preferably the residue of a copolymer consisting of units derived from ethylene oxide and propylene oxide or the residue of a polysiloxane consisting of di-C 1-4 alkylsiloxane units.
- the ethyleneoxide/propylene oxide copolymers may be represented by formula I ##STR3## in which R 2 is hydrogen or has, independently, the same meaning as R 1 above, and p, q and r are numbers from 0 to 100 with the provisos that at least one of p, q, and r is at least 1, and that q>p+r.
- Preferred polysiloxanes correspond to formula II ##STR4## in which q has the same significance as previously mentioned.
- H is the residue of a polypropylene glycol having from 10 to 200 units derived from propylene oxide.
- the copolymers of the invention contain at least 12, preferably from 18 to 40 structural units of formula I, i.e. n is preferably a number from 18 to 40. This means that the sum of m+n preferably is a number from 25 to 60.
- the acid groups of the copolymers with structural units of formula I may be in free acid or salt form. These salts may be alkali, alkaline earth, ferrous, aluminum, (alkanol)ammonium or (alkyl)ammonium salts. Preferably these copolymers are in the form of alkali metal salts, particularly sodium salts.
- the copolymers correspond to the formula ##STR5## wherein M, R, R 1 , x, y, z, m and n are as defined above and Y is hydrogen, an alkali or alkaline earth metal ion, ferrous ion, aluminum ion, (alkanol)ammonium ion or (alkyl)ammonium ion,
- Organic copolymers with structural units of formula I may be produced by methods well know in the art, for example, by reacting a random copolymer of the following composition ##STR6## with a compound of formula III
- the reaction of the maleic acid anhydride groups in the styrene--maleic anhydride copolymer shown hereinabove with compounds of formula I or II and III may be substantially complete, or there may remain in the final polymer a number of anhydride groups which will form dicarboxylic acid groups in aqueous solution. A 100% transformation which theoretically can be obtained with equimolar amounts of the reactants will, of course, never be achieved.
- Copolymers of the type described hereinabove are obtained by copolymerization of styrene and maleic acid anhydride and are well known and are described for example in C. E. Schildknecht, "Vinyl and Related Polymers” John Wiley and Sons, Inc., New York, 1952.
- Polyalkylene glycols of formula I or III are also well-known compounds and may be obtained by addition of alkylene oxides, especially ethylene oxide and propylene oxide to alkyl- or cycloalkylalcohols or phenols, or by polyaddition of the alkylene oxides.
- the polysiloxanes of formula II are also well-known compounds and may be obtained, for example, by the polycondensation of dichlorodimethylsilane with chlorotrimethylsilane and water.
- the new copolymers with recurring units of formula I are excellent surfactants and may be used to disperse organic and inorganic materials. In particular, they may be used as additives for cementitious mixes.
- cementitious mixes in which the organic copolymers of the invention may be used as additives, are mortars and concretes.
- the hydraulic binder may be Portland cement, alumina cement or blended cement, for example, pozzolanic cement, slag cement or other types, Portland cement being preferred.
- the organic copolymers of the invention are added in amounts of from 0.01 to 10%, preferably from 0.1 to 3% by weight based on the weight of the cement.
- the organic copolymers of the invention have the property of fluidifying the cementitious mixes to which they have been added and are therefore excellent superplasticizers. They have the additional advantage of having a degree of air entraining properties which is lower than those of similar copolymers suggested for use in such applications, e.g. the copolymers covered by U.S. Pat. No. 5,158,996.
- Cementitious mixes comprising the SMA copolymers of the present invention exhibit excellent physical properties in the hardened concrete, e.g. high strength.
- the solution is heated to 140° and 12.83 parts of a polyalkylene glycol sold under the trade name "Pluronic" PE 6100 is added over 5 minutes. The temperature is maintained and the mixture is stirred for a further 2 hours. After cooling to about 60°-70°, the solution is diluted with 235 parts deionized water. After cooling to room temperature, the emulsion is neutralized with about 28.5 parts of sodium hydroxide solution (30%) and adjusted to a solids content of 40%.
- the polyethylene glycol serves as a solvent at 100° and is esterified with the copolymer of maleic acid anhydride and styrene at 140°.
- Polyethylene oxide 6100 has a molar mass of the propylene oxide block of 1750 g/mol and a percentage of polyethylene oxide of 10%.
- Polyethylene oxide polyethylene oxide block has a molar mass of the propylene oxide block of 950 g/mol and a percentage of polyethylene oxide of 10%.
- Polynperonic PE L-61 is a block copolymer of propylene oxide and ethylene oxide having a molar mass of 2090 g/mol.
- “Dowfax” 20 A 64 is a block copolymer of propylene oxide and ethylene oxide having a molar mass of 7209 g/mol.
- “Dowfax” 20 A 612 is a block copolymer of propylene oxide and ethylene oxide having a molecular weight of 1000.
- “Synalox” 50-50B is a random copolymer of propylene oxide and ethylene oxide having a molar mass of 1200 g/mol,
- Synalox 100-150 D is a random copolymer of propylene oxide and ethylene oxide having a molecular weight of 2750.
- “Synalox” 100-D95 is a polymer of propylene oxide having a molecular weight of 2000.
- CC-118 is a butylether of the block copolymer of 27 mol propylene oxide and 4 mol ethylene oxide.
- CD-115 is a block copolymer of propylene oxide and ethylene oxide with methylether and hydroxy end groups,
- the molar mass of the propylene oxide block is 1900 g/mol and the percentage of polyethylene oxide is 5%.
- VP 1610 is a polydimethylsiloxane with hydroxy propylene end group having a molecular weight of 650.
- SLM 50400/61 is one with hydroxy pentamethylene end group having a molecular weight of 3000.
- SLM 50400/62 is one with hydroxypropylene end group having a molecular weight of 3000.
- SLM 50480/6 is a polydimethylsiloxane with hydroxypropylene end group which is etherified with 10 ethylene oxide groups and having a molecular weight 1400.
- a mortar is mixed in accordance with DIN 1164, Part 7 with the following constituents: 1350 g of well-mixed standard sand, 450 g Portland cement and 180 g tap water.
- the tap water contains 0.3% of the compound of Example 1, calculated as dry matter on the weight of cement.
- the mortar is mixed according to standard conditions, and immediately after mixing the consistency of the mortar is determined according to DIN 1060, Part 3; DIN 1048, Part 1 or any other standard method.
- the same mixes are prepared but without any admixture, or containing a condensation product of naphthalene sulfonate or melamine sulfonate and formaldehyde using the same dosage (0:3% by weight of dry matter, based on cement). From the results of testing it can be seen that the fluidity characteristics of the mortar of the invention is much better than those of the comparative mortar.
- the mixing is performed in a ribbon blender, the water being added within the first 30 seconds and the mixing continued for a total of 2 minutes.
- a comparative concrete mix containing a condensation product of naphthalene sulfonate and formaldehyde is prepared. In both cases, 0.3% by weight of the admixture, based on cement, is added to the mixing water. After mixing, the fluidity of the fresh concrete is determined, either according to ASTM C 143 (slump) or according to DIN 1048 (flow table). Concrete mixes containing an admixture of the invention exhibit better consistency and fluidity than do comparative mixes without or with conventional admixtures.
Abstract
Description
R.sub.1 --O--(--R--O).sub.m --H (III)
______________________________________ "Pluronic" PE 6100 (BASF) "Pluronic" PE 3100 (BASF) SYNPERONIC PE L-61 (ICI) DOWFAX 20 A 64 (DOW) DOWFAX 20 A 612 (DOW) SYNALOX 50-50 B (DOW) SYNALOX 100-150 D (DOW) SYNALOX 100-D95 (DOW) CC-118 (Nippon Oil & Fats) CD-115 (MBT) ______________________________________
______________________________________ VP 1610 (Wacker) SLM 50400/61 (Wacker) SLM 50400/62 (Wacker) SLM 50480/6 (Wacker) ______________________________________
______________________________________ mesh 1 mm 20% mesh 4 mm 45% mesh 8 mm 70% mesh 16 mm 100% powder content 8% ______________________________________
Claims (22)
R.sub.1 --O--(--R--O).sub.m --H (IV)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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US08/471,544 US5612396A (en) | 1990-12-29 | 1995-06-06 | Copolymers |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
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DE4042182 | 1990-12-29 | ||
DE4042182.1 | 1990-12-29 | ||
US81402091A | 1991-12-26 | 1991-12-26 | |
US10896193A | 1993-08-18 | 1993-08-18 | |
US27270994A | 1994-07-08 | 1994-07-08 | |
US08/471,544 US5612396A (en) | 1990-12-29 | 1995-06-06 | Copolymers |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US27270994A Continuation | 1990-12-29 | 1994-07-08 |
Publications (1)
Publication Number | Publication Date |
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US5612396A true US5612396A (en) | 1997-03-18 |
Family
ID=27435095
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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US08/471,544 Expired - Fee Related US5612396A (en) | 1990-12-29 | 1995-06-06 | Copolymers |
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US (1) | US5612396A (en) |
Cited By (45)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5798425A (en) * | 1995-04-07 | 1998-08-25 | Skw Trostberg Aktiengesellschaft | Co-polymers based on oxyalkyleneglycol alkenyl ethers and unsaturated dicarboxylic acid derivatives |
US5985989A (en) * | 1997-07-09 | 1999-11-16 | Arco Chemical Technology, Lp | Method of making a water reducing additive for cement |
US6043329A (en) * | 1997-04-07 | 2000-03-28 | Cement Intellectual Property Ltd. (Cip) | Acrylic copolymers |
US6063184A (en) * | 1996-04-12 | 2000-05-16 | Mbt Holding Ag | Admixtures for cementitous compositions |
US6211299B1 (en) * | 1998-03-24 | 2001-04-03 | National Starch And Chemical Investment Holding Corporation | In situ solvent free method for making anhydride based graft copolymers |
WO2001042161A2 (en) | 1999-12-10 | 2001-06-14 | Mbt Holding Ag | Water-soluble air-controlling agents for cementitious compositions |
WO2001042162A1 (en) | 1999-12-10 | 2001-06-14 | Mbt Holding Ag | Solubilized defoamers for cementitious compositions |
US6267814B1 (en) | 1998-08-14 | 2001-07-31 | Mbt Holding Ag | Cementitious dry cast mixture |
US6290770B1 (en) | 1998-08-14 | 2001-09-18 | Mbt Holding Ag | Cementitious mixture containing high pozzolan cement replacement and compatabilizing admixtures therefor |
US6310159B1 (en) * | 1998-01-20 | 2001-10-30 | The Dow Chemical Company | Low foaming paper surface sizing composition |
US6310143B1 (en) | 1998-12-16 | 2001-10-30 | Mbt Holding Ag | Derivatized polycarboxylate dispersants |
US20030127026A1 (en) * | 2001-11-05 | 2003-07-10 | James Edward Anderson | High early-strength cementitious composition |
US20030144385A1 (en) * | 1999-07-09 | 2003-07-31 | Vickers Thomas M. | Oligomeric dispersant |
US20030187100A1 (en) * | 1999-12-10 | 2003-10-02 | Mbt Holding Ag | Water soluble air controlling agents for cementitious compositions |
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